136581
1,5-Diazabicyclo[4.3.0]non-5-ene
98%
Synonym(s):
DBN
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About This Item
Empirical Formula (Hill Notation):
C7H12N2
CAS Number:
Molecular Weight:
124.18
Beilstein:
2417
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
Quality Level
Assay
98%
form
liquid
refractive index
n20/D 1.519 (lit.)
bp
95-98 °C/7.5 mmHg (lit.)
density
1.005 g/mL at 25 °C (lit.)
SMILES string
C1CN=C2CCCN2C1
InChI
1S/C7H12N2/c1-3-7-8-4-2-6-9(7)5-1/h1-6H2
InChI key
SGUVLZREKBPKCE-UHFFFAOYSA-N
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General description
DBN is a strong base widely used as a catalyst in organic synthesis to facilitate Michael additions and aldol condensations.
Application
1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) can be used as:
- A reagent for the synthesis of β-carbolines from tetrahydro-β-carbolines via dehydrogenative/decarboxylative aromatization.
- A nucleophilic organocatalyst in the regioselective C-acylation of pyrroles and indoles by Friedel−Crafts acylation reaction.
- A superbase in the formulation of a ternary liquid-liquid phase changing system, along with hexadecane and hexanol, to capture hydrogen sulfide gas.
- A base for the preparation of 1H-quinazoline-2,4-diones from 2-aminobenzonitriles using supercritical carbon dioxide as a reactant and a solvent.
- A catalyst for the synthesis of benzothiazolones by the reaction between 2-aminothiophenols and CO2 by cyclocarbonylation reaction via C-S bond formation.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Skin Corr. 1B
WGK
WGK 3
Flash Point(F)
201.2 °F
Flash Point(C)
94 °C
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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The simple solvent-free synthesis of 1H-quinazoline-2, 4-diones using supercritical carbon dioxide and catalytic amount of base
Mizuno T, et al.
Tetrahedron Letters, 45(38), 7073-7075 (2004)
Organic base-promoted efficient dehydrogenative/decarboxylative aromatization of tetrahydro-βcarbolines into β-carbolines under air.
Zhao Z, et al.
Tetrahedron Letters, 60(11), 800-804 (2019)
Phase-Change Reversible Absorption of Hydrogen Sulfide by the Superbase 1, 5-Diazabicyclo [4.3. 0] non-5-ene in Organic Solvents.
Xu Z, et al.
Industrial & Engineering Chemistry Research, 58(4), 1701-1710 (2019)
Ryuichi Arakawa et al.
Journal of mass spectrometry : JMS, 40(1), 66-69 (2004-12-08)
When elemental selenium was added to a strongly basic amine, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), the selenium started to dissolve and the solution turned dark brown. We investigated the chemical reaction of this selenium dissolution process by electrospray ionization mass
Organic Base-Catalyzed C-S Bond Construction from CO2: A New Route for the Synthesis of Benzothiazolones.
Gao Xiang, et al.
Catalysts, 8(7), 271-271 (2018)
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